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Located on the Chesapeake Bay on Maryland’s Eastern Shore, the small town of St. Michaels has a rich maritime history and there’s no better time to experience that history than the crisp, cool days of fall. October is filled with events that the whole family will enjoy.

Boat lovers should plan to come to the Chesapeake Bay Maritime Museum on the first weekend of October, Friday the 4th and Saturday the 5th, for the annual Mid-Atlantic Small Craft Festival. This is one of the country’s most popular boat-building festivals, where you can see hundreds of unique canoes, kayaks, and sail boats from amateurs and professionals alike. The event is free for museum members; tickets for non-members are $15 for adults, $12 for seniors, and $6 for kids age 6-17.

St. Michaels holds their annual fall festival two weeks later, on Saturday the 19th and Sunday the 20th. Come to the Community Center on Saturday 10:30am-7pm for pumpkin carving and pie baking contests and view the scarecrows in their own contest all over the town. On Sunday head over to the St. Michaels Inn for Jack Russell terrier races. Registration opens at 10am, the races begin at 11am. All major events are free.

Come on back to the Chesapeake Bay Maritime Museum on the last Saturday of October, the 26th, for OysterFest. Here you can sample a variety of oyster-based delicacies as well as other local foods, enjoy live music, craft beer, and river cruises, or learn from demonstrations of regional activities. Hours are 10am-4pm; tickets are $5 for adult museum members; non-member prices are $18 for adults, $15 for students and seniors, and $6 for children age 6-17.

On any of these Saturdays, you can also visit the farmer’s market in the parking lot at 204 S. Talbot St., explore the Classic Motor Museum at their Cars and Coffee event (free), or learn about the spooky stories in the history of St. Michaels on a ghost walk. Ghost walk tickets are $20 for adults, $15 for kids age 8-12, and must be purchased in advance. Meet at the entrance of the Chesapeake Bay Maritime Museum at 7pm. While you’re in town be sure to visit the CBMM’s special photography exhibition On Land and On Sea: A Century of Women in the Rosenfeld Collection.

With all of these awesome fall events, you will want somewhere to lay your head at night after a full day of exploring St. Michaels. You’re in luck as there are a wide array of lodging options including quaint bed and breakfasts like Wades Point Inn on the Bay and cozy vacation rental cottages and homes.

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